Imidazolidin-1-oles, N-2-aminoethyl nitrones and 1,2,5-oxadiazinanes. A novel ring-chain tautomerism

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dc.authorscopusid7004177880
dc.authorscopusid35080000800
dc.contributor.authorCoşkun, Necdet
dc.contributor.authorAsutay, Oktay
dc.date.accessioned2022-05-11T14:47:08Z
dc.date.available2022-05-11T14:47:08Z
dc.date.issued2007
dc.departmentMeslek Yüksekokulları, Muratlı Meslek Yüksekokulu, Kimya ve Kimyasal İşleme Teknolojileri Bölümü
dc.description.abstractImidazolin-3-oxides I were reduced with NaBH4 in THF at reflux to give the corresponding 2,3,5-triarylimidazolidin-l-oles 2, which are proved to be in a ring-chain-ring tautomeric equilibrium with N-2-aminoethyl nitrones 3 and 3,5,6-triphenyl-1,2,5-oxadiazinanes 4. The ratios of the ring and chain form are determined by the substituent at the reaction centre and can be described by the equation logK(x) = p sigma(+) + logK(x=H). These are the first examples of a novel three-component ring-chain-ring tautomeric equilibrium characterized by a Hammett-type equation. The stability of the ring form was favoured by electron-withdrawing substituents. Treatment of the equilibrium mixture of 2, 3 and 4 with phenylisocyanate in refluxing toluene gives selectively the corresponding O-carbamoylated imidazolidines 5; cis-5 was shown to isomerize to trans-5 on heating. (C) 2007 Elsevier Ltd. All rights reserved.
dc.identifier.doi10.1016/j.tetlet.2007.05.058
dc.identifier.endpage5155
dc.identifier.issn0040-4039
dc.identifier.issue29en_US
dc.identifier.scopus2-s2.0-34250325972
dc.identifier.scopusqualityQ3
dc.identifier.startpage5151
dc.identifier.urihttps://doi.org/10.1016/j.tetlet.2007.05.058
dc.identifier.urihttps://hdl.handle.net/20.500.11776/10439
dc.identifier.volume48
dc.identifier.wosWOS:000247995900043
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.institutionauthorAsutay, Oktay
dc.language.isoen
dc.publisherPergamon-Elsevier Science Ltd
dc.relation.ispartofTetrahedron Letters
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectnitrones
dc.subjectrearrangement
dc.subjectimidazoline
dc.subjectimidazoline-3-oxides
dc.subjectring-chain tautomers
dc.subjectConversion
dc.titleImidazolidin-1-oles, N-2-aminoethyl nitrones and 1,2,5-oxadiazinanes. A novel ring-chain tautomerism
dc.typeArticle

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